32 Regrettable ’90s Guys Fashion Trends

Nobody ever pulled off JNCOs.

1. Overalls with one strap down.

Overalls with one strap down.

View this image ›


Nothing said, “I’m a badass not a farmer,” like having one strap down on your overalls. In reality you just looked like you were one of the Little Rascals.

2. Hip-Hop Looney Tunes T-shirts.

Hip-Hop Looney Tunes T-shirts.

View this image ›

Via ebay.com

AKA the most “urban” gear a lot of kids from the suburbs ever wore.

3. Skechers Chrome Dome.

Skechers Chrome Dome.

View this image ›


The shoes that put Skechers on the map! It’s oh-so-mid ’90s design was a weird cross between a hiking shoe and a sneaker. Plus, they were also chunky!

4. Middle part bowl cuts.




Literally looking like a butthead.

5. Oakleys Eye Jacket sunglasses.

Oakleys Eye Jacket sunglasses.

View this image ›

Via forums.watchuseek.com

Probably the most coveted sunglasses for guys in the ’90s — they were also terribly unflattering. Unless you wanted to look like a bug.

6. Backwards baseball hats.

Backwards baseball hats.

View this image ›

Via social.entertainment.msn.com

Literally, from 1990-2000, the only people who could read your hat were the people behind you.

7. Hemp necklaces.

Hemp necklaces.

View this image ›

Via craftstylish.com

These were basically the ’90s equivalent of chokers for guys; except they were incredibly itchy and the wooden beads would painfully press-up against your Adam’s apple.

8. Caesar cuts.

Caesar cuts.

View this image ›


We can all blame George Clooney for this trend.

9. Flannel tees/ Plaid short-sleeve shirts.

Flannel tees/ Plaid short-sleeve shirts.

View this image ›

Via kidsinthe90s.tumblr.com

Ugly plaid wasn’t just for flannels thanks to these short-sleeved shirts.

10. Hoop earrings.

Hoop earrings.

View this image ›

Via plushiegalaxyz.com

Yo-ho, yo-ho, a pirate’s life for ’90s me!

11. Bowling-inspired shirts.

Bowling-inspired shirts.

View this image ›


Could these shirts have BEEN anymore big and shapeless? Also, you could probably blame Swingers for the rise in popularity of these shirts.

12. Socks with shower sandals.


And the sandals had to be Nike or Adidas, no exceptions.

13. Kangol hats.

Kangol hats.

View this image ›

Paramount Pictures / Via pattygopez.buzznet.com

The ultimate cool guy hat, which, let’s be honest, you thought you could wear with anything. For school? Yup! For date night? For sure! For a wedding? Duh, it looks fly with a suit. The reality, Samuel L. Jackson is the only living person who can successfully pull off a Kangol hat.

14. Fanny packs.

Fanny packs.

View this image ›

Via etsy.com

I mean, what else were you supposed to carry your pogs and Game Boy in?

15. Pagers.


View this image ›

Via tumblr.com

The ultimate baller-status accessory. Of course, it was important that you clip it on the outside of your pants so that everyone knew you had one. Maybe you even kept it safe and looking extra stylish by attaching it to your pants with a chain.

16. Wale cords.

Wale cords.

View this image ›

Via wordpress.com

The perfect way to let everyone know you were coming by the not-so-subtle zoosh sound they made as you walked.

17. Overly baggy jeans.

Overly baggy jeans.

View this image ›

Via adamchristopherr.tumblr.com

If ’90s guys had one style motto when it came to pants it would be: THE BAGGIER THE BETTER. Of course, you also looked ridiculous walking around with pants so big that they were difficult to even keep up.

18. Levi’s “Button Your Fly” shirts.

Levi's "Button Your Fly" shirts.

View this image ›

Via bim.shopstyle.com

Who thought this was funny? Oh yeah, the same dudes who rocked those Looney Tunes T-shirts.

19. Acrylic striped ski sweaters.





These sweaters weren’t just hot and itchy, they were also not the greatest quality (no matter how much you paid for them). They usually looked pretty ratty due to the horrible amount of pilling they would get — after wearing them just once!

20. Big, fat, chunky skate shoes.

Big, fat, chunky skate shoes.

View this image ›

Via insidemycar.tumblr.com

Which you probably wore without ever setting foot on an actual skateboard.

21. Fat laces.

Fat laces.

View this image ›

Big-tongued chunky sneakers needed equally as big laces to go with them.

22. Bucket hats.

Bucket hats.

View this image ›

Via wordpress.com

The perfect accompaniment to that windbreaker you got at the thrift store to complete your On Golden Pond look.

23. White crew neck T-Shirts under everything.

Time & Life Pictures



A blindly white T-shirt was a ’90s essential whenever you wore a button-up or V-neck.

24. Vertical striped button ups.




Were these supposed to make us look taller or something? The appeal is lost on me now.

25. Velcro wallets.

Velcro wallets.

View this image ›

Via tactics.com

Who needed a leather wallet? This was the perfect place to keep that old condom you carried around.

26. Cross Colours.

Cross Colours.

View this image ›

Via thesymmetricswan.com

The fashion equivalent of Skittles.

27. Carpenter jeans.

Carpenter jeans.

View this image ›


Basically these were just jeans that came with an extra loop on the hip for you to put your hammer in.

28. Big Johnson T-shirts.





The T-shirt for bros, before there was even a word for “bros.”

29. Mandarin collars.

Mandarin collars.

View this image ›

Via popcultureidiot.blogspot.com

They should be called “Mandar-outs,” amirite?

30. Starter Jackets.

Starter Jackets.

View this image ›

Via fullmetalstarterjacket.tumblr.com

The best thing to wear when you wanted to look like you put on 25 pounds. Also, the jacket was incredibly noisy thanks to the whoosh-whoosh sound you made whenever you moved your arms.

31. Rayon shirts.

Columbia Pictures



“I know what guys will like! Silky printed shirts that are made from synthetic fiber! Quick, call the ’90s and tell ‘em we’re coming!” – Person who created these fashion fails.

32. Frosted tips.


Dimension Films


Have you seen the awful photos of Justin Timberlake with frosted tips? Yes. Well, the sad truth is that frosted tips looked even worse on you.

Read more: http://buzzfeed.com/briangalindo/regrettable-90s-guys-fashion-trends